p-Toluenesulfonic acid → HCID 15520896, compound

HRID 565139Notes

Reaction equation

HRID 565139 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[NH2:8][CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].CC1C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>>[C:10]([CH2:9][NH:8][CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 409140Benzyl glycinate

Product 1

HCID 15520896HCID 15520896, compoundYield 73%

Procedure

Ethyl acrylate (24.4 mL, 225 mmol) and glycine, benzyl ester, p-toluenesulfonate (50.0 g, 148 mmol) were combined in a 250 mL round bottom flask. With stirring, triethylamine (24.8 mL, 178 mmol) was added via syringe and the reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was partitioned between ethyl acetate (660 mL) and 10% aqueous Na2CO3 (300 mL). The organics were washed with water (100 mL) and saturated NaCl (100 mL). The organics were dried over MgSO4, filtered and concentrated in vacuo followed by pumping under high vacuum to yield N-(carbobenzyloxymethyl)-3-aminopropionic acid, ethyl ester (39.3 g, 73% yield) as a yellow oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 22 hours
  2. customThe reaction mixture was partitioned between ethyl acetate (660 mL) and 10% aqueous Na2CO3 (300 mL)
  3. washThe organics were washed with water (100 mL) and saturated NaCl (100 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43c5cb258b7e4a08aa68a7c7ce545058
Source dataset
uspto-grants-2001_01
Patent number
US06171578B2

Reaction notes

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